


With A Little Help From My Friends

by WorldOfDemons



Series: Learning Lessons [2]
Category: Supernatural
Genre: Dean instruction Cas, F/M, Voyeur!Sam - Freeform, bit of a praise kink for Cas, i'd really love to be the reader here
Language: English
Status: Completed
Published: 2015-07-22
Updated: 2015-07-22
Packaged: 2018-04-10 14:59:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,247
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4396358
Author URL: https://archiveofourown.org/users/WorldOfDemons/pseuds/WorldOfDemons
Summary: <blockquote class="userstuff">
              <p>Sequel to Just a Little Practice<br/>Dean decides that Cas still needs some instruction and you are more than happy to help.</p>
            </blockquote>





	With A Little Help From My Friends

**Author's Note:**

> So in the comments section of Just a Little Practice, we decided that we needed a sequel. That sequel turned into a two day straight project which is now the longest piece I've ever written. I'm so happy with the way it turned out and I hope y'all are too! 
> 
> **Title taken from the song by Joe Cocker.

 

You went straight to your room in the bunker after the _pleasurable_ ride with the boys. You honestly didn’t know how you were supposed to feel after what Cas did to you, knowing Dean was watching and guiding. And Sam – you collapsed on your bed, still dirty from the hunt. You groaned at the thought of Sam jacking off to your moans. Determined to try and forget the way the boys made you feel, you grabbed some pajamas and hit the shower.

 

You felt better after a hot shower. You were dressed in a pair of cotton shorts and a big t-shirt. You were rubbing a towel through your hair as you came back to your bedroom. You pushed open the door and stopped.

“Hey, Y/N.” Dean was sitting on your bed and Cas was pacing nervously at its foot. You leaned against the doorframe.

“Something I can help you boys with?” Dean smirked. He leaned back on his arms and dangled his legs over the edge of your bed.

“Well, you see Y/N,” Dean started. “I have this little problem.”

“Little?” you smirked at him. He nodded.

“And what does Cas have to do with this ‘problem’?” You made air quotes around your words. His head snapped up and his stopped pacing at the mention of his name. You looked back at Dean who was grinning.

“My problem is that I think Cas need some more help. I mean - we didn’t even get all the way in the car. I also think he needs more _hands on_ instruction. Maybe even a demonstration.”

Your eyebrows shot up. The events in the car were hard enough for you, but going all the way with not one but both of them? It was tempting and the heat growing in your abdomen was getting tough to ignore.  You stepped fully into the room and closed the door behind you.

“And what _exactly_ does Cas need help with?” Your voice dropped low and you crossed the room towards Cas. He looked down at you as you moved close to him until you were pressed against his chest.

“Don’t kiss her, Cas.” Dean said. Cas looked over at Dean surprised. Dean pulled his legs up and crossed them underneath him.

“Calm down, big boy. You’ll get there eventually. First, take her face in your hands.” His voice dropped low. “Look into her eyes, don’t break eye contact.” Cas cupped your face in his calloused hands. He moved closer to you, his deep blue eyes boring into yours. His forehead pressed into yours. Some how just that small touch made you start to breathe heavy. Cas must have noticed the change in breathing and smiled. You could see his initial nervousness fade and the Cas from the Impala came drifting back.

“You ready to kiss her?” Dean asked. Cas nodded. “Start slow.” Cas’ forehead pulled off of yours and he leaned in closer. Gently he pressed his lips to yours. One of his hands moved from your face and to the back of your head. Your arms wrapped around his neck and his other hand fell to your waist. His tongue probed at your closed mouth begging for entrance. You allowed him in and gave control to him. He explored your mouth. You eventually pulled back for breath.

“How have you gotten better in the past half hour?” You breathed. He smiled and almost imperceptibly his eyes flicked to Dean.

“Have you been practicing, Castiel?” You whispered. He ignored you and leaned back in to kiss you again. You pushed his trench coat off his shoulders until it hit the ground. His hands moved down your body and rested on your waist. You started tugging at his dark blue tie.

“I don’t think I told you to start undressing yet.” Dean said. You could hear the smirk in his voice. You pulled away from Cas.

“Fuck you, Winchester.” You leaned back into Cas. You heard your bed squeak and felt Dean press himself to your back. His hands pushed Cas’ off your waist and replaced them with his own.

            “Get more creative with your hands, Cas.” Dean whispered. “But I think we need a different position.” Dean took a few steps back and sat down on the bed. He pulled you with him. He sat back with his legs spread out. He positioned you with your back against him nestled between his legs. He bent your legs and held you under your knees. He buried his face in your neck kissing and sucking marks on your skin. Cas kneeled in between your legs. His hands slid up your shirt.

            “Let me take it off.” He said. You weren’t sure if he was talking to you or Dean, but you nodded and Dean moaned against your heated skin. Cas slowly raised your shirt, stopping to leave a line of kisses up your stomach as he pulled it up. Slowly he pulled the shirt over your breasts and over your head. You hadn’t put on a bra after your shower, Cas smiled as he made the discovery. He pulled you away from Dean and kissed you again as he took your breasts in his hands. Dean whined at the loss of you and leaned forward to find you again.

You continued your tugging at Cas’ tie until you managed to pull it off. His jacket was next as you desperately undressed him. His rough fingers kneaded your sensitive breasts running his fingers over you nipples. He gently pulled on them and you moaned into his mouth. Dean continued to kiss up your neck until he settled on a spot below your ear. Dean’s hands moved down your waist and rested between your legs gently on your cloth-covered center.

“You ready to get rid of these very annoying shorts?” Dean whispered in your ear. You nodded and Cas groaned as you pulled away. You shifted so Dean could slowly pulled your shorts down your legs your panties sliding with them. Cas softly sighed taking the sight of you in. You leaned back against Dean’s chest as he opened you up for Cas.

“You never get tired of it. Just looking at her.” Dean muttered. Not to you or Cas specifically, but Cas nodded in agreement anyway. He gently ran his hands up your legs.

“So it seems we had some trouble finding your clit last time, Y/N.” Dean said. “Figured we’d remedy that problem.” He pressed a kiss to your temple.

He grabbed one of Cas’ hands and pulled it off your leg. Dean steered his hand toward your exposed center. You gasped at the combined touch of their hands, Dean’s covering Cas’.  Dean guided their hands and used Cas’ fingers along your slit. Your head fell back against Dean’s shoulder.

“Get her nice and warmed up.” Dean whispered. Their fingers intertwined, you couldn’t tell who was who.

“One finger in.” He breathed. You felt a finger – you guessed it was Cas – gently probe at your center. You whimpered at the small touch and the finger slowly pushed inside you. You resisted the urge to buck your hips against the slow moments. You pulled your head up to look down at Cas. He was focused, his finger pumping in and out of you. Dean guided Cas to add another finger.

“Bit faster.” He whispered. Cas’ eyes flicked up to your face. He was still unsure of himself despite Dean’s assistance. You smiled down at him and nodded. Your head fell back again as he sped up and slipped a third finger in. Dean began to kiss your neck again, but kept his eyes on you and Cas.

“You think you can take four?” he whispered in your ear. You felt another finger slip inside you – Deans. Together they stretched you, not uncomfortably but you weren’t as full as you wanted to be.

“I need you.” You whispered. You didn’t know who you were talking to, but you need grew quickly. Dean chuckled behind you.

“You’ll have to hold on a bit, sweetheart. We’re just getting started.” You moaned at the thought of waiting. Dean pulled his finger out of you and pulled Cas out at the same time. You quietly whined as you lost their touch. Dean grabbed Cas’ hand again

“Clit.” He said simply. He used Cas’ fingers to explore you until finding the sensitive bud.

“Shit,” you whispered as he made contact. Dean moved Cas’ fingers in small, light circles. He took Cas’ other hand and slid two of his fingers back into you. Dean pushed Cas’ fingers in and out of you as Cas continues to stroke your clit. Your breathing grew labored as you felt your orgasm grow.

“I’m close.” You said.

“Let’s try this,” Dean said. He withdrew Cas’ hands from you.

“Dean…” you started.

“Hush.” He said simply. He reached around your body and grabbed Cas’ face gently. He led Cas’ head down to meet your aching center. Tentatively, he stuck his tongue out and licked along your slit.

“Cas,” you cried out. You reached down and twisted your hands into his short hair. His dark blue eyes looked up at you.

“You like that, don’t you Cas.” Dean said from his spot behind you. “You like pleasing Y/N. And you’re so good at it.”

Cas moaned and his tongue probed deep inside you. You gasped and your hips jerked up. Dean quickly moved his hands to your hips and held you down. Cas closed his eyes and focused on you.

“Be still, Y/N.” Dean said. Somehow you nodded and tried to keep still. You gasped as Cas found your clit and began to gently suck.

“Cas,” you breathed. He opened his eyes again and pulled up from you.

“Use my full name.” He growled, his voice deep and rough. You remembered back to the car. He liked hearing you say his name, not his nickname.

“Say it.” He said. “Every syllable.” He dipped his head back down to you.

“Castiel,” you pleaded. Dean had to fight to hold you down; you were bucking against him. Cas attached his mouth around your clit and began to suck gently. Dean wrapped an arm around your waist and kissed your neck again. You were going to be covered in bruises for days. A gentle finger once again pushed inside you. You pushed back against Dean.

“I’m not going to last much longer.” You groaned. Cas gripped your legs tightly.        

“Let go, Y/N. Come for us.” Within seconds, you were coming crying out for Castiel. You collapsed against Dean panting.

“Cas,” you started. He raised his eyebrows at you. “Castiel,” you corrected yourself. “If you’re just learning, I can’t wait to know what you’re like as a master.” Dean laughed.

“He did good didn’t he?” Dean muttered into your ear. You nodded. Cas smiled at Dean’s words.

Dean pulled you up to where you were sitting by yourself.

            “Well, I guess it’s time for Cas to learn how to fuck a girl properly.” Dean picked you up and tossed you further back on the bed. Dean crawled on top of you his arms forming a cage around your head. He leaned in and roughly kissed you. His touch was so different from Castiel’s.  He was rougher; he knew exactly what he wanted, exactly what you wanted, and exactly how to give it to both of you. Your arms wrapped around his neck and he deepened the kiss. When he pulled away you were both panting. He rolled off of you and climbed off the bed.

            “Get him undressed.” He headed toward the door.  “I’ll be right back.” He flung open the door and left. He turned and stuck his head back in the room.

            “Oh, Y/N, get him good and hard.” He winked and disappeared again.

You crawled to the end of the bed and pulled Cas closer to you. You pushed his suit jacket off and began to unbutton his shirt. As it fell to the ground you slowly ran your fingers down his chest. You leaned in and pressed gentle kisses to his abdomen. You looked up at him as you unbuttoned his pants and pulled them down his legs. He stepped out of them and you got up from the bed. You turned him around and pushed him onto the bed. You palmed his growing member through the boxers he was wearing. Slowly, you pulled them off of him revealing his cock. You threw the fabric over your shoulder with a smirk.

            “You ready?” you asked. You wrapped your hand around his base gently. He nodded. You smiled.

            “Alrighty, then.” You started moving your hand up and down. His eyes closed and he struggled to breath. You ran your thumb over his sensitive tip. His mouth dropped and a moan slipped out. He jumped when you slipped the head of his cock into your mouth. He groaned as took more of him until he hit the back of your throat.

            “Y/N,” he groaned. He buried his hands in your hair as you bobbed your head sucking hard. Cas began panting.

            “Y/N, I’m close.” You looked up at him through your lashes. His face was twisted in pleasure. Dean chose that exact moment to walk in.

            “Easy, Y/N.” Dean had gotten rid of his shirt while he was gone. “Don’t make him cum quite yet.” He smirked and you pulled your mouth off of Cas’ member with a pop. Your lips were slightly swollen from kissing Dean and sucking off Cas. You stood up and Dean motioned for you to climb on the bed. He tossed something to Cas. Dean must have explained how to put a condom on before because he didn’t have any problems. Or maybe he just had some experiences with condoms but not with women. You made a mental note to ask about that.

            You positioned yourself back at the head of the bed with Cas following you. You both assumed a similar position, as you and Dean were earlier. But where Dean was rough, Cas was gentle. One arm held him up and the other lovingly held your head.

            “You ready?” Cas whispered. You smiled.

            “I think the real question is are _you_ ready.” You felt Cas line himself up at your entrance.

            “Hold up, Cas.” Dean stopped him. “Don’t just jump straight in.” He climbed up onto the bed and settled behind Cas.

            “Let me help you.” He muttered his mouth close to Cas’ ear. Oh there was definitely something going on there. Dean reached around Cas and grabbed his cock.

            “Tease her first.” He slid Cas’ cock up and down your slit. Your eyes closed and your breathing became jagged.

            “Make her beg for it. Start small.” He slipped just the head of Cas’ member into you. You bucked against him craving more.

            “Be still, Y/N.” Dean ordered. You struggled but obeyed.

            “Please, Dean.” You moaned. Dean released his hold on Cas’ cock.

            “Don’t beg me.” He crawled around and positioned himself next to your head.

            “Beg Cas.” He said. Your eyes opened as you look at the angel kneeling between your legs.

            “Please Castiel.” You cried. He pulled out of you completely. You whined quietly then realized your mistake.

            “Castiel,” he slipped his tip back into you. “Castiel, please.” You gasped. He slowly drove himself into you. Finally, he was completely sheathed in you. Your hands flew up and gripped the headboard.

            “Castiel,” you begged. “Please.”

            “Please what?” Cas reached down and kneaded your breast.

            “Please fuck me.” Cas leaned down and pressed a kiss against your still slightly swollen lips.  

            “Your wish is my command.” He started moving slowly, gently, but with a certain force and presence that only Cas could have. You gasped as Cas began to speed up.

            “Castiel,” You groaned. “Fuck,” Dean reached down and stroked your hair gently.

            “He’s doing good, isn’t he baby.” He muttered loud enough for both of you to hear. You whimpered and nodded. Dean crawled back around to Cas.

            “You hear all those beautiful little noises she’s making? You love it, don’t ya?” Dean ran his fingers through Cas’ dark hair. Cas nodded.

            “You’re doing so good. Keep up what you’re doing, but try teasing her clit while you’re going.” Cas followed Dean’s instruction and reached down and gently put pressure on your clit before starting to rub small circles.

            “Oh fuck,” you moaned.

Footsteps sounded down the hall. Before anyone realized that the door was still open from when Dean left, Sam had made his appearance.

            “Hey, Y/N, have you heard of… holy shit.” Sam dropped the book he had been doing research from. Dean looked up to the door and grinned.

            “Hiya, baby bro. Just giving Cas some more instruction. You got any helpful tips you care to share?” Sam snapped out of the trance he was in. He picked up the book he dropped and quickly crossed the room dropping the book on your desk as he passed it. He crawled onto the bed on the other side of you. Gently he cupped your face his thumb rubbing small circles across you cheek. Without moving his hand, he glanced down to where Cas was disappearing into your body.

            “Fuck,” he whispered. Dean looked over to his brother.

            “You really get off on that, don’t you?” With a glazed look in his eyes, Sam nodded. Dean smiled then turned his attention back to you and Cas.

            “Try a bit harder, Cas. She can take it.” Without verbally acknowledging Dean, Cas began to push into you harder until your were hanging on the edge of climax. Sam leaned down and kissed you silencing the moans and profanity falling out of your mouth. Finally, after what seemed like an eternity, you pulled away from Sam and came hard at the same time as Cas. You collapsed and fell against the bed breathing heavy. Cas leaned against Dean for support and he pulled him so his was relaxing against his bare chest. Dean reached up and ran his fingers through Cas’ hair.

            “You did so good. Made Y/N feel so good.” Cas’ head fell against Dean’s shoulder. He nodded. He looked exhausted. Dean gently maneuvered him so that he was lying down beside you. He turned his attention back to you. He shoved Sam’s hand off your face and replaced it with both of his on either side. He leaned in close to you his lips barely brushing yours.

            “You think you can handle round two?” He whispered. One of his hands dropped down and rested between your legs. You bit you bottom lip considering. You were still incredibly sensitive, but you weren’t about to turn down being fucked by Dean Winchester.

            “Besides,” Dean continued. “Sammy didn’t get to see the entire show. And now that we know how it affects him…” he trailed off leaving the rest up to your very capable imagination. You smiled at his implications and nodded your consent. He pressed a kiss against your lips. You felt Cas roll over onto his side so he could get a better view. You also heard Sam quietly swear and he began to pull his clothes off. You opened your eyes through the kiss and saw him pull off his thin t-shirt. You took in his tanned chest. Dean’s touches slowly became rougher as he deepened the kiss. Your eyes closed again as you tried to focus on Dean. He gently bit your bottom lip as he pulled away. There was a playful glint in his eyes as moved away from you. He slowly began to kiss his way down your body. His eyes flicked up at you as you buried your hands in his short hair. He finally reached your center where he hovered, making you wait. You pushed yourself up and propped up on your elbows.

            “Dean,” you said. You were about to threaten him when his mouth made contact with your aching heat.

            “Oh my god, Dean.” You gasped. His tongue dipped deep into you hitting every inch that you craved. Cas wasn’t bad for someone new, but Dean knew exactly what he was doing from years of experience. Your eyes wandered to Sam who had a death grip around his cock.

            “You like what you see?” You muttered to him. His eyes were filled with lust as he nodded slightly. Dean attacked your clit with his mouth and you fell back against the bed. When you managed to open your eyes, you found Sam’s face again. You could see the struggle in his head. Watching your face twist in ecstasy or watch was his brother was doing to your body. Dean didn’t spend much time with you. He quickly made his way back up your body.  He leaned down and pressed a kiss to the side of your head.

            “Forgive me, but I’m not going to take this slow.” He whispered. He pressed his forehead against yours.

            “And I’m not going to be gentle.” He moved you so that you were sitting up slightly against the headboard. He bent your legs so that they were on either side of his body. He twisted a hand behind your head. You felt his member prod at your opening.

            “Dean,” you whispered. He smiled and pulled his head away to look at you.

            “Beg for me.” He said simply. You wanted to roll your eyes, but your desire lost in competition to your pride.

            “Please, Dean.” You pleaded. “I need....” You started, but gasped as he slid his cock up and down along your slit.

            “Need what, sweetheart? Tell me exactly what you need, Y/N.” His hands ghosted over your body, barely touching.

            “Shit, Dean.” You breathed. “I need you. I need your cock inside me. I want you to fuck me so hard that I won’t be able to walk tomorrow.” He slipped the tip of his cock inside you.

            “Is this what you want? Do you like being watched by Sam and Cas?” You reached up and grabbed the headboard.

            “Yes,” you moaned. Slowly he sunk into you. He began to pull himself in and out of you. He pulled you against his chest his hands flat against your back.

            “You want me?” You nodded. You didn’t trust yourself to speak and bit your lip to hold in the sounds that were trying to escape. He stopped his thrusts. Dean moved his hands off your back and cupped your face. You wobbled on his lap – his cock still buried inside you.

            “Don’t you dare hold back a single sound from me. I know what I can do to you. And I know that I can make you scream. And, Y/N – I’m going to do it.” His lips crashed into yours and you both fell back against the bed. He grabbed your wrists and pinned them above your head. Your hips bucked against his as he slammed into you. You wrapped your legs around his waist trying to find an angle where he hit you deeper. Dean chuckled and leaned in towards you.

            “You’re not in control here, dear.” He whispered in your ear. You could only moan in response.

            He pushed you harder than anyone had ever pushed you before. Your mind went blank. You couldn’t really think about anything but Dean. You were aware of Cas watching and Sam jacking off – both of them sitting so close. The familiar pressure began to build in you.

            “Fuck, Y/N. Jesus fucking Christ.” Dean moaned. He was getting close too. “You gonna come, gorgeous? You gonna cum all over my cock?” His breathing was ragged and his thrusts becoming desperate. You’re entire body was overcome by electricity as you came around his cock. You could feel Dean coming even though he remembered to put on a condom. He pulled out of you and sat back between your legs.

You tried to sit up, but Sam pushed you back down.

“I’m going to cum all over you, Y/N.” He grunted before shot his load on your stomach and chest. You ran a finger through the cum that coated you. Sam grabbed your wrist and quickly stuck the digit in his mouth. The sight of him sucking his cum off your finger elicited another groan from you.

“Sam, that is so fucking hot.” You said.

After a few seconds of recovering from his climax, Sam grabbed his clothes from where he tossed them on the floor. He quickly pressed a kiss to your temple and left. Dean settled down in the space that he left in the bed while Cas moved on top of you capturing your lips gently. He used his angel powers to zap pajama pants onto him and Dean and an oversized t-shirt on to you after cleaning Sam’s cum off of you.

He pressed his forehead against yours.

“Thank you, Y/N.” He whispered. You smiled and cupped his face.

“You’re so welcome, Castiel. If you ever feel like you need more experience, just give me a call.” He smiled and you gently pushed him off of you. You sat up, propped on your elbows. You smirked and looked at the two stunning men on either side of you.

“Now, I do believe you both owe me an explanation on exactly how close you two are and how you got that way.”


End file.
